How to Hire a Content Writer: An Interactive Roadmap for Busy Founders and Marketers

It’s only your brand messaging, no big deal. Just the thing investors, clients, and Google judge you on. So maybe your accountant’s cousin, “who’s kind of getting into marketing,” is not the best choice for this job. Who is though? Let’s find them.

Hiring a content writer is one of the most strategic decisions you’ll make for your business. The writer you bring in won’t just describe what your business does. They’ll shape how investors perceive you, how clients trust you, and how regulators interpret your messaging. A missed nuance could cost your business deal flow or trigger an expensive compliance audit.

However, most companies don’t actually know how to hire a writer. At least, not one who can handle their complex messaging, technical language, and high-stakes audiences. Unfortunately, when you don’t know how to hire a content writer, you risk more than boring blogs. 

You risk publishing white papers that contradict your own legal disclaimers, sales decks that confuse the pitch instead of closing it, and brand messaging that creates more questions than confidence.

We see it most in highly technical, regulated industries:

• Healthcare organizations are struggling with HIPAA-compliant messaging. 

• Manufacturing firms are trying to turn technical specs into investor-friendly language. 

• Real estate investors are in high-stakes meetings with pitch decks written in generic startup speak. 

• Software companies are building brilliant products no one outside the dev team understands.

• Engineering firms are pitching cutting-edge infrastructure with sentences that sound like they were debugged, not written.

None of these teams need more content. They have plenty. It’s just not working for them. Instead, they need the right content written by a professional writer who actually understands their space.

At Borrowed Pen, we specialize in writing for complex, regulated, and credibility-driven industries. Our clients don’t come to us because they need words. They come to us because they need to land enterprise deals, earn investor trust, convert high-value leads, or get their marketing copy through regulatory audits.

In this guide, we’ll walk you through how to hire a content writer who actually gets your business and creates high performing content. You’ll learn how to prepare for the hire, what questions to ask them, how to spot red flags, and how to build a real content marketing partnership that pays off in ROI, not rewrites.

Step One: Know What You’re Actually Hiring For

You’re not hiring for words. You’re hiring for impact.

Before you post a job or DM your designer’s cousin who “does copy on the side,” take a step back. You need to know what kind of writer you’re hiring and more importantly, what kind of writing your business actually needs.

Not all writers do the same thing. A ghostwriter for your thought leadership posts is not always going to be the same person who will write your technical white papers or UX microcopy. Here’s how to determine which writing professional you need to hire.

Determine What Kind of Content You Actually Need

Start by inventorying your content needs. Consider if you need:

• Website Copy: Are you updating your homepage, about page, or service pages?

• Thought Leadership: Do you need a ghostwriter for LinkedIn posts, op-eds, or bylined articles?

• Sales Enablement Materials: Think case studies, one-pagers, pitch decks, and email sequences.

• Technical or Regulated Content: Product specs, whitepapers, documentation, or anything that would make a legal team sweat.

• SEO-Driven Blog Posts: Keyword-optimized, strategic blogs to rank and convert.

• Email or Funnel Copy: Nurture sequences, onboarding flows, and campaigns that drive action.

• Investor and Internal Communications: Executive summaries, fundraising decks, quarterly updates, board memos, and company-wide comms.

• Event and Conference Copy: Speaker bios, panel descriptions, session titles, signage, promo blurbs, and recap blogs.

• Product Marketing Copy: Feature announcements, release notes, product pages, in-app messages, and GTM content bundles.

• Product Descriptions and Feature Copy: Detail-rich, conversion-optimized copy for ecommerce, marketplaces, SaaS, and hardware.

• Ad Copy and Social Snippets: Short, high-conversion copy for paid ads, carousels, and shareable content across channels.

• Podcast and Video Content: Show notes, host scripts, guest prep guides, social cutdowns, recaps, and teaser copy.

• Customer Education Materials: Help docs, onboarding tutorials, training decks, and video scripts.

  
  

ACTION STEP: MAP YOUR CONTENT

Make a quick content map. List all the types of writing you need over the next 6 - 12 months. Ask yourself:

• What formats do you need? 

• What goals would you like to achieve?

• What audiences would you like to reach?

  
  

Borrowed Pen Tip: Don’t Just Hire for Format. Hire for Function.

Let’s say you need a white paper. That’s the format. However, the function might be to generate leads, inform investors, or support a compliance review. A good content writer understands the strategic purpose behind every piece and tailors the writing accordingly.

A Real World Example: At Borrowed Pen, when a client asks us for a “case study,” we start by asking what the study needs to achieve. 

• Is it a trust builder for enterprise clients? 

• A sales enablement tool for reps? 

• A content asset to gate for lead gen? 

We write differently based on your goal because “case study” is the format, but outcome is everything.

Know the Role You’re Actually Hiring

Here’s a breakdown of common writer roles (and how to pick the one you need):

Writer Type	What They Do
Content Writer	Blogs, articles, white papers, SEO writing
Copywriter	Ads, product copy, landing pages, CTAs
Technical Writer	Manuals, specs, highly structured regulated content
Ghostwriter	Writes as you, for thought leadership and bylined content
Content Strategist	Defines messaging architecture, content strategy, and workflow

QUIZ: WHAT KIND OF WRITER DO YOU NEED?

For each line below, check all that apply:

• We need help figuring out what to say, not just how to say it.

• We want someone to write in the founder’s voice.

• We need copy that converts leads, not just fills a page.

• We operate in a regulated industry or complex vertical.

• Our internal team doesn’t have time to give constant feedback.

Results:

• If you checked 3 or more, you need a strategic content writer, not a task-taker.

• If you checked “regulated” or “founder’s voice,” you need someone with specialization not just a portfolio of lifestyle blogs.

• If you checked “no time for feedback,” you need someone who proactively manages the process, not just deliverables.

Why Knowing What You Need Matters

You’re not hiring for a blog post. You’re hiring for business results. When you know what kind of content you actually need, you avoid mismatched hires, missed goals, and expensive rewrites. A little clarity upfront means a stronger brief, a faster process, and content that actually performs.

Step Two: Prep Before You Post

Great content in, great content out. Prep = ROI.

As with any project, successful content writing requires thoughtful preparation. 

If you want writing that drives business, a little upfront prep makes all the difference. You don’t need a massive brand bible or a deck longer than your favorite Netflix binge. What you do need is a clear sense of your goals, who you’re talking to, and the message you actually want to land. That’s what helps great writers do their best work. 

When you line those pieces up, hiring clicks into place, strategy gets sharper, and your content starts carrying its weight (and then some). Here’s how to set yourself up before you kick off the search.

1. Define the Business Goal of the Content

Every content project should serve a business objective. If you don’t know what that is, your writer will have to guess. Ask yourself “am I…

• Trying to drive traffic?

• Improve lead quality?

• Convert prospects?

• Educate stakeholders?

• Reduce friction in your sales process?

• Translate technical specs into investor-friendly language?

  
  

ACTION STEP: DEFINE YOUR OBJECTIVES

For every type of content you want, write down the business objective next to it. No vague goals allowed! “Brand awareness” is not a functional KPI unless you’re tracking it.

2. Get Your Brand Messaging in Check

Writers are not psychic. You need to provide clear brand positioning. Content writers always need to know: 

• Who are you speaking to?

• What makes you different?

• What do you want people to believe, feel, or do after reading your content?

• What tone should the writing take? (Confident? Curious? No-nonsense?)

  
  

Borrowed Pen Tip:  Start With What You Have

If you don’t have a messaging guide, that’s okay. Gather what you do have. Pull past marketing copy, brand decks, internal memos, founder rants. We’ve turned napkin scribbles into brand platforms. Just give us something to work with.

3. Organize Your Raw Materials

To give your writers real context into your brand, gather corporate documents like:

• Internal strategy docs

• Product or service overviews

• Customer personas

• Sales decks

• Competitor benchmarks

• SME recordings or interviews

• Any compliance or regulatory guidelines

ACTION STEP: BUILD THE BRIEF

Create a single folder called “Writer Brief.” Put all relevant materials in there. Add a doc that answers the basic who/what/why/how questions about your content goals.

4. Set Expectations Around Scope, Process, and Timeline

Here’s where most content projects go off the rails: Lack of clarity around how you’ll work together. Get clear on:

• How many rounds of feedback?

• What’s your preferred review process?

• Who signs off?

• What’s the timeline for delivery and approval?

• Are you expecting the writer to upload to your CMS? Provide SEO meta data? Source images? Conduct interviews?

Jargon-to-English Translator: When you say “SEO blog,” do you mean 300 words with keywords, or a 2,000-word conversion-optimized piece with internal linking and content strategy? Let’s define the terms and we’ll get better returns. 

ACTION STEP: DO A TEAM GUT CHECK

If this writer will be working with multiple departments (marketing, product, legal, and the CEO who likes to rewrite things at midnight), make sure everyone is aligned on expectations.

TEAM TALK TEMPLATE:

• What does success look like for this content project?

• Who needs to review the writing?

• What kind of feedback is most helpful vs. distracting?

• What’s our tone not supposed to sound like?

ACTION STEP: CREATE A PRE-HIRE CHECKLIST

Here’s what to prep before you start booking discovery calls with agencies like Borrowed Pen:

✔ Define your business goals for content 

✔ List specific deliverables you need 

✔ Identify your audience (real data > assumptions) 

✔ Clarify internal review and approval process 

✔ Get stakeholder alignment on tone and voice 

✔ Set a realistic timeline and budget 

✔ Know what “success” looks (conversions, authority, reach, etc.)

Why Prepping Before You Hire A Content Writer Matters

By doing the prep work, you make the hire smoother, the work better, and the partnership stronger. You’re not just hiring a writer. You’re investing in a content asset. The more prep you do, the more ROI you get.

Step Three: Spot the Right Writer (and Dodge the Duds)

If you feel seen, so will your ICP.

You’re prepped. You’re organized. You’ve got your content goals and a beautifully labeled folder (or at least one that isn’t called “FINAL_v7_ACTUALLYFINAL.pdf”). Now what?

It’s time to find a writer who actually gets your business. Not just someone who can string words together but someone who can take raw information, business strategy, and complex input from multiple stakeholders… and still deliver content that performs.

Unfortunately, most people don’t know what a good writer looks like until they’ve been burned by a bad one. Let’s fix that.

What to Look For in a Content Writer

1. Strategic Thinking:  

You want someone who asks smart questions about your goals, audience, and funnel, not someone who just asks, “How many words?”

2. Industry Translation Skills: 

Can they take legal, financial, healthcare, or manufacturing speak and turn it into content that works for the actual reader whether that’s a customer, regulator, or CFO?

3. Content Marketing Know-How

Do they really understand SEO, buyer journeys, content purpose, CTAs, and funnel stages? Or are they just hoping you won’t notice?

4. Strong Portfolio (That’s Relevant) 

It’s not about style. It’s about the outcome. Look for work that resembles what you need: Byline or ghostwritten, technical or brand-forward, and long-form or short. Bonus points if they’ve written for businesses like yours.

5. Process Fit

If your internal team is Type-A about approvals and timelines, don’t hire a writer who “just vibes it out.” Ask about their workflow. A great writer should have a reliable process and tell you how they like to collaborate.

Watch Out For These Red Flags When Hiring A Content Writer

• They agree to everything without pushing back. Good writers challenge vague directions and ask questions that make your content stronger. If they’re just nodding along? That’s not collaboration, that’s content apathy.

• They promise “fast and cheap.” You want thoughtful, strategic, informed. That takes time. “Fast and cheap” gets you copy that reads like a fortune cookie translated from a PDF.

• They’ve never heard of your industry and don’t ask about it. Writers don’t need to be experts in your niche, but they should be interested enough to research and ask smart questions. Curiosity is a minimum requirement.

ACTION STEP: WRITE YOUR INTERVIEW QUESTIONS

Use this section to start building your list of content writer interview questions: 

• Can you walk me through your research and writing process?

• What do you need from us to do your best work?

• Have you written for [industry type] before? If not, how would you approach it?

• How do you handle multiple stakeholders with conflicting feedback?

• How do you define content success?

• What happens if the first draft misses the mark?

Why Hiring The Right Writer Matters

“How would you explain what we do to a 10-year-old, a client, and a journalist?” If they can hit all three? Hire them immediately.

ACTION STEP: RUN A TEST PROJECT

Not ready to sign a retainer? Run a paid trial, but do it with purpose.

1. Pick a necessary project 

2. Provide a strong brief 

3. Offer feedback and assess how they handle it

4. Evaluate both the content and the collaboration experience

Borrowed Pen Tip: Consider The Work-Style Litmus Test

A strong trial project should leave you thinking: “This is exactly how I want to work.” If it leaves you feeling like you just babysat a freelancer, move on.

Why Hiring The Right Writer Matters

You’re no longer hiring based on gut feelings or “good vibes.” You’re assessing strategic, technical, and collaborative fit. The person you bring in shouldn’t just write well. They should make your business better.

Step Four: Set Your Writer Up for Success

Writers aren’t mind readers. (If only we were…)

The best content happens when your writer has what they need to actually deliver. We need your messy drafts, the old decks, the founder stories, and the little quirks that make your brand sound like you. The more we see, the faster we can zero in on your voice.

Setting your writer up for success doesn’t just make the work stronger. It makes the whole process easier and a lot more fun. Instead of endless rewrites, you get drafts that land closer to the mark, faster collaboration, and content you actually look forward to publishing (and reading yourself!).

When the setup is solid, working with a writer stops feeling like a chore and starts feeling like momentum. You get the relief of knowing your story is in good hands, and we get to do what we do best: 

Make your brand sound like the sharpest version of itself. Here’s what to prep for your content writer. 

What Writers Need From You

1. A Clear Brief 

The writer is not a mind reader (though we have worked with some suspiciously intuitive ones). A good brief should include:

• Objective: What’s the content supposed to achieve?

• Audience: Who’s reading this and what do they care about?

• Format: Blog, white paper, pitch deck, landing page (each one has different rules.

• Voice and tone: Buttoned-up? Bold? “Speak like our founder but without the swearing”?

If you don’t have a formal brief template, Borrowed Pen has one. Just ask (or steal ours and pretend it’s yours). We’ll allow it.

2. Background Materials 

Sadly, this is where most content goes to die. Give them:

• Brand messaging frameworks (positioning docs, style guides, etc.)

• Existing content assets

• Sales collateral, pitch decks, FAQs

• Access to internal SMEs (even if it’s a single call)

• Performance data, if available (top-performing blogs, bounce rates, etc.)

3. One Point of Contact 

Decision-by-committee is where content dreams go to get watered down and stripped of voice. If five people are reviewing copy, make sure feedback is consolidated and clear. Otherwise, your writer ends up editing in circles and charging you for the loop.

4. Defined Approval Process 

Deadlines are easier to hit when everyone agrees on what “done” means. Set expectations for:

• Number of rounds of edits

• Turnaround times

• Final signoff flow

  
  

A strong process turns “I don’t like it” into the more effective “Let’s revise for this specific goal.”

Why Setting Your Writer Up For Success Matters

You’re not just hiring a content writer. You’re building an ecosystem where good content can thrive. Your process, input, communication, and feedback loops need to work. Skip this, and even the best writer will deliver disappointing results. Nail this, and your ROI skyrockets.

Step Five: Build a Long-Term, High-ROI Relationship

Build something that lasts

You’ve found the right writer and the content is landing. Your leads are warmer, your brand sounds sharper, and you no longer have to explain what your company does to blank stares. That’s momentum and it’s worth investing in.

Content is a competitive advantage that compounds over time, especially when the partnership behind it grows alongside your business.

When your writer truly understands your customers, your industry, and the way your team talks when the Zoom call ends, everything clicks. Strategy gets smarter. Execution moves faster. Your content starts connecting dots across the funnel instead of just filling space.

You’re not just buying copy, you’re buying growth. Let’s fuel it.

Why Long-Term Writers Outperform One-Off Hires

1. Institutional Knowledge Grows Over Time 

A writer who’s worked with you for 6+ months understands your voice, your market, your internal politics, your customer objections, and what you meant when you said “let’s make it punchier.” That context creates exponentially better content.

2. They Can Anticipate Needs 

When your writer knows your product roadmap, launch cycles, and sales bottlenecks, they stop reacting and start proactively suggesting what to write next. You get stronger messaging and fewer scramble moments.

3. You Build Brand Consistency 

Your tone, structure, vocabulary, and positioning will all be cohesive. Consistency is hard to pull off when you’re constantly swapping freelancers and re-explaining who your audience is. Long-term writers create alignment, not just assets.

4. It Saves You Money (Yes, Really) 

Writers who are deeply embedded in your business need less handholding, make fewer mistakes, and require fewer revisions. That means fewer billable hours and better results.

What to Invest In for the Long-Term

Ongoing Strategy Touchpoints

Treat your writer like a marketing partner. Loop them into quarterly planning, product updates, and big-picture shifts. You’ll get content that supports your growth goals instead of lagging behind them.

Performance Reviews (the good kind)

Review what’s working. Share analytics, feedback from sales, lead gen results. Writers love data. It helps us write smarter. A quarterly retro is all it takes.

Content Calendars

Don’t live draft to draft. Plan 1–2 months ahead, so your writer isn’t chasing deadlines and you’re not settling for filler. Shared calendars, Trello boards, or a Notion page (it doesn’t have to be fancy, just functional).

Open Communication 

Give real feedback. Celebrate what’s working. Flag red flags early. Writers aren’t fragile. We just want to know what’s actually helping you grow.

How to Be a Client Writers Want to Stick With

Great writers are in high demand. Want to keep yours? Treat them like a partner, not a gig worker. Here’s how:

Borrowed Pen Tip: How to Be a Dream Client

Want better writing? Be a better partner. Here’s what that looks like:

• ✅ Assign one internal lead for content projects

• ✅ Use a consistent content brief template

• ✅ Gather and share existing materials before kickoff

• ✅ Agree on timelines, process, and feedback loops

• ✅ Provide timely, consolidated feedback that connects to goals

• ✅ Treat the relationship like a collaboration not a transaction

ACTIVITY STEP: MAKE A PARTNER PLEDGE

Look at your best vendor relationships. What makes them last? Now write a 3-sentence “partner pledge” for your content writer. Make it real by sticking it in your onboarding doc.

Why Building A Long Term Relationship Matters

Hiring a content writer scales your voice, expands your reach, and increases your influence in the market. If you treat the relationship like a strategic investment, and not just a line item, you’ll get content that actually moves the needle.

If you want content that performs, builds trust, and survives a compliance review, you need a writer who gets your business. (Hey, we know someone.)

What Should You Do Next?

You're not just hiring a writer. You're building a partnership. So here’s how to put everything you’ve learned into action.

Hire Like You Mean It

If you've made it this far, you're already ahead of most companies. You're not looking to slap some SEO keywords into a blog post and call it a day. You want strategic, high-performing content that actually does something, whether that’s moving your audience, converting leads, closing deals, or avoiding lawsuits. (All equally noble goals.)

At Borrowed Pen, we write content for people who think deeply, build boldly, and need copy that keeps up. We translate complexity into clarity. We shape brand voice around credibility, not clichés. And we do it with language that actually makes people want to read more, even when the subject matter is dryer than toast in the Sahara.

Book A Call With Borrowed Pen

If you made it through this checklist and realized, “Wow, we need someone who can handle complex ideas and make them fun to read,” we should talk.

Book a discovery call. We’ll ask smart questions, listen closely, and if it’s the right fit, we’ll help your brand finally say what it means and mean what it says.

Your ideas deserve better than buzzwords. Let’s write something that works.

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Keep reading for more resources to prepare before our call:

Quiz: Are You Ready to Hire?

Grab a pen or hey, borrow ours and answer these questions to make sure you’re ready to reach out:

1. Do you know what you need written? 

☐ Yes, I have specific content in mind 

☐ Sort of, I have a general idea but need help shaping it 

☐ No, but I know I need something

2. Do you know who your audience is? 

☐ Yep, we’ve got personas, data, and real insights 

☐ Kinda, we know the industry, but not specifics 

☐ Not really, our audience is “everyone,” we guess?

3. Do you have a clear voice or brand messaging? 

☐ Yes, it’s documented and consistent 

☐ Sort of, we go by vibes 

☐ No, what’s a brand voice again?

Scoring:

• Mostly top checkboxes? You’re ready.

• Mostly middle? You’re almost there.

• Mostly bottom? Time for a brand strategy sprint.

Activity: Brand Voice Stress Test

Think of this like CrossFit for content. You’re going to run three of your most important brand messages through a little obstacle course to see if a writer can actually match your tone, maintain your credibility, and not make you sound like an AI-generated LinkedIn post from 2014.

Step 1: Choose Three Messages You Say Often

Examples:

• “We’re a results-driven agency that partners with sustainable manufacturers.”

• “We help investors close deals faster through better marketing.”

• “We write HIPAA-compliant copy that doesn’t make people fall asleep.”

Step 2: Try Rewriting Each One in These 3 Ways:

1. Plain English: Explain it like you would to a client in conversation.

2. Your Brand Voice: Rewrite it how your brand should sound.

3. Wrong Voice: Do a parody version: too formal, too casual, too robotic, or full of buzzwords.

Step 3: Use It in Interviews

Ask your candidate to rewrite these three lines in your preferred tone or even better, give them a sample and ask why they’d change it. A great writer should be able to explain their voice decisions, not just make copy “sound nice.”

Quiz: Are You Content-ROI Ready?

Our quick check will tell you if you’re setting your writer (and your ROI) up for success.

Check all that apply:

☐ We know how to measure success (conversions, deals, trust, compliance).

☐ We track what’s working and actually share results with our writer.

☐ We set aside a real budget for content, not just “whatever’s left.”

☐ We treat content as a revenue driver, not a side project.

☐ We want writing that builds value over time, not just one-and-done pieces.

Results:

• 4–5 boxes checked: You’re running content like an investment. ROI ahead.

• 2–3 boxes checked: You’re on the right track, just tighten up your goals.

• 0–1 box checked: You’re still funding content like coffee money. Time to level up.